Michael Masterson is not your typical businessman. An ex Peace Corps volunteer, he never took a class in business, doesn’t read the business press, and doesn’t like to talk business. He spends his spare time writing poetry, collecting fine art, and practicing Brazilian Jiu Jitsu. His neighbors call him a bohemian. But he’s also an entrepreneur. He started his first business when he was 11 years old, and in the 45 years that have elapsed since then, he has started or co-started dozens of successful businesses – public and private ... local and international ... retail, wholesale, and direct mail.

His entrepreneurial experience is immense, even compared to other successful entrepreneurs. At one time or another, he has run or consulted for multimillion-dollar businesses in all of the following areas:

information publishing

investment advice

health, healing, and nutrition

bars and restaurants

retail furniture

fine art sales

painting, carpentry, and pool construction

public relations

career advancement

costume jewelry

perfumes and cosmetics

personal accessories

baby products

audiotape programs

magazines, newsletters, and books

international real estate development

rental real estate management

sports and fitness

Richard Schefren, founder of the business coaching company Strategic Profits, says, “I consult with all of the best-known entrepreneurs in the world, and I’ve never known anyone who has been in more different sorts of successful businesses than has Michael Masterson.”

Katie Yeakle, director of American Writers & Artists Inc., puts it this way: “You’ve heard of the serial entrepreneur. Michael Masterson is a polygamous entrepreneur. He is not satisfied with owning one single successful business at a time and then going on to another. If he’s not having lunches with at least six CEOs a month, he’s just not happy.”

Michael bristles at Yeakle’s assessment. “I have had a problem with entrepreneurial addiction in the past,” he says. “But I’ve kicked the habit. When I turned 50, I promised my wife I wouldn’t start another company. And I’ve kept to that promise.”

Don’t tell that to Dr. Al Sears, whose business, Wellness Research & Consulting Inc., was begun with Michael’s help in 2006 and grew from nothing to $4 million in less than 24 months. “The pace at which we became successful was remarkable and rewarding. A good part of the credit goes to Michael,” he says.

When asked about his involvement in Wellness Research, Michael blushed. “Oh, that,” he said. “That doesn’t count. I wasn’t a partner. It’s just a once-a-month luncheon thing. I don’t consider that ‘starting a new business.’”

The last business Michael admits to having helped launch is EarlytoRise.com, an Internet-based company that provides advice and training in “health, wealth, and wisdom.” Started initially as an informal weekly e-mail to a handful of his protégés, it quickly morphed into a $20 million enterprise.

Michael serves as a consultant and chief expert on entrepreneurship for EarlytoRise.com, which features dozens of business and investment experts – including, according to Michael, “lots of guys much smarter than me.”

The primary focus of his business life these days, however, is split between real estate and consulting for his primary client, Agora Inc., a $300 million, Baltimore-based publisher of information products with offices in England, France, Spain, Germany, South Africa, and Australia. “It’s an honor to be associated with Bill Bonner (Agora’s founder and CEO) and this company,” Michael says. “And a pleasure to have been part of its growth.”

Notwithstanding clandestine luncheons that erupt into new multimillion-dollar ventures, Michael insists that he has been spending most of his time teaching and writing since he retired, for the second time, when he turned 50. “I have wanted to be a writer since my father complimented me on the first poem I wrote. I was, I think, 12,” he says. “There is nothing I like better than spending three or four hours in the morning writing, and then spending the rest of the day reading, wrestling, and going to museums and art galleries with my wife.”

He writes poetry and fiction (“somewhat badly,” he says), as well as books on business and wealth building (all of which have been Wall Street Journal, Amazon.com, or New York Times best-sellers). “I have a readership that appreciates the way I look at things,” Michael says. “And that is gratifying.”

His non-fiction books include Seven Years to Seven Figures: The Fast-Track Plan to Becoming a Millionaire, Automatic Wealth for Grads…and Anyone Else Just Starting Out, Automatic Wealth: The Six Steps to Financial Independence, Power and Persuasion: How to Command Success in Business and Your Personal Life, and Confessions of a Self-Made Millionaire.

Michael’s first business was selling his booklet, Excuses for the Amateur, to fellow fifth-grade students when he was 11. In addition to this early entrepreneurial effort, he worked afternoons and evenings as a paper boy and in a car wash, for a sliver polisher, in a warehouse, as a busboy, and as an aluminum-siding salesman. It wasn’t easy growing up with seven brothers and sisters in a working-class neighborhood in New York. His father, a teacher at a private Catholic college, had an annual salary of only $12,000. Besides working in his spare time to contribute to the family’s income, Michael wore hand-me-down clothes and grew up in “the poorest family on Maple Avenue” – which, he says “wasn’t on the other side of the tracks … it was on the tracks.”

Michael doesn’t complain about how difficult his childhood was. On the contrary, he says he was privileged. “It gave me good values, lifelong friends, and the impetus to go out into the world and make some money. How can I complain about that?”
On the other hand, he admits that when he read Frank McCourt’s memoir, Angela’s Ashes, he thought, “So what’s the big deal?”

In college, after working for $6 an hour one summer installing aboveground swimming pools, Michael and two friends started their own company, doing the same thing. Working 15 hours a day for $30 an hour, he was suddenly making more money than he could spend. “That was a first for me,” he says. “And I liked it.”

During the winter, when it was too cold to build pools, Michael supplemented his income by tending bar and painting houses. “After that, I never had to rely on a single income,” he says. “It became a habit, one that was hard to break.”

Michael continued to hold jobs and run side businesses throughout college and grad school. And then he quit everything and joined the Peace Corps. As a volunteer in Chad, he published his first book, taught at the university, and spent his spare time learning to speak French and play rugby.

He later landed a job in Washington, D.C., writing and producing newsletters while working on a Ph.D. and teaching. A move to South Florida was next – and an experience he had there while he was editorial director of a financial newsletter-publishing company in the early 1980s changed his life.

It happened at a Dale Carnegie success course, “How to Win Friends and Influence People,” which he wound up in by a twist of fate. He had meant to enroll in a public-speaking course to help with some of his job responsibilities – but there he was. And though he was initially cynical, he started to work the program – beginning by critically examining his life goals ... and then choosing one that would be his primary objective.

After mulling over scores of possibilities, he came to the realization that making “being wealthy” his number-one goal would put the rest of them at his fingertips. He also realized that working for other people was not going to get him there.

After making this decision, which he calls one of the most important he has ever made, Michael put all his efforts into becoming wealthy.

His first step was to learn all he could about the business he was already in – publishing and marketing newsletters. Soon he had produced an entirely new type of newsletter, with an accompanying direct-mail promotion, and convinced his boss to cut him in on the profits it brought in. He had to mortgage the equity in his home to get that cut, but Michael’s stake in the newsletter was worth $1.5 million a year later. He was at the beginning of a very lucrative and successful business career.

As a partner in that publishing company, Michael shepherded its rise from a $100,000 to a $135 million business.

At the age of 33, Michael created the Oxford Club, the most successful financial advisory ever, with an international network of thousands of investors.

At 39, he retired for the first time, wrote fiction (including a film script that was optioned, 12 short stories that were published, and a novel that was not), and bought an art gallery “for the fun of it.”

A year later, he joined one of his former competitors in the newsletter business and helped bring that company from $8 million to more than $300 million in 15 years.

In the early 1990s, he began working with partners to test out ideas about small-business development. More than a dozen of the businesses they launched became multimillion-dollar ventures. Two saw revenues in excess of $20 million.

At the same time, he began investing in real estate, both in luxury home developments and apartment complexes. Within 10 years, he owned multimillion-dollar properties and projects all over the world.

When he turned 50, he tried to retire for the second time. Unsuccessful once again, he started EarlytoRise.com, which has grown, in less than seven years, into a highly profitable, $20 million business that serves more than 200,000 customers.

These days, Michael is determined to work as little as possible. “The problem,” he says, “is that I don’t know the difference between work and play. If it makes me happy, I want to do it. Am I crazy?”

Ready, Fire, Aim is his tenth book and fifth with John Wiley & Sons. His next projects are a collection of poetry, a screenplay, and a book of short stories, all of which will be published next year. He continues to write about starting and developing small businesses on a weekly basis in the EarlytoRise.com e-zine.